Evaluation of gem-Diacetates as Alternative Reagents for Enzymatic Regio- and Stereoselective Acylation of Alcohols
Dominik Koszelewski*, Anna Brodzka, Arleta Madej, Damian Trzepizur and Ryszard Ostaszewski*
*Institute of Organic Chemistry Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warszawa, Poland, Email: dominik.koszelewskiicho.edu.pl, ryszard.ostaszewskiicho.edu.pl
D. Koszelewski, A. Brodzka, A. Madej, D. Trzepizur, R. Ostaszewski, J. Org. Chem., 2021, 86, 6331-6342.
DOI: 10.1021/acs.joc.1c00154
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Abstract
Benzylidene 1,1-diacetate is a sustainable and efficient acyl donor for enzymatic acylation of chiral and nonchiral alcohols. Especially, unsaturated acetates can be converted without E/Z isomerization. The acyl donor can be recreated and reused. A dynamic kinetic resolution (DKR) protocol results in chiral acetates in high yields and very high enantiomeric excesses.
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Key Words
Acetates, Acylation, Asymmetric Acylations of Alcohols
ID: J42-Y2021